(Pyridin-4-yl)boronic acid → HCID 59759984, compound

HRID 1693132Notes

Reaction equation

HRID 1693132 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([F:17])=[CH:14][CH:15]=2)[C:10]([CH3:18])=[C:9]1[S:19](=[O:33])(=[O:32])[NH:20][C:21]1[CH:26]=[CH:25][C:24](Br)=[CH:23][C:22]=1[C:28]([F:31])([F:30])[F:29])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1>COCCOC.C(O)C.C(=O)([O-])[O-].[Na+].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([F:17])=[CH:14][CH:15]=2)[C:10]([CH3:18])=[C:9]1[S:19](=[O:33])(=[O:32])[NH:20][C:21]1[CH:26]=[CH:25][C:24]([C:37]2[CH:38]=[CH:39][N:34]=[CH:35][CH:36]=2)=[CH:23][C:22]=1[C:28]([F:31])([F:30])[F:29])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 2

HCID 2734379(Pyridin-4-yl)boronic acidHCID 59759981HCID 59759981, compound

Product 1

HCID 59759984HCID 59759984, compoundYield 53.9%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

This compound was prepared in analogy to Example 2 starting from 2-(4-bromo-2-trifluoromethyl-phenylsulfamoyl)-5-fluoro-3-methyl-indole-1-carboxylic acid tert-butyl ester (0.108 g), 4-pyridineboronic acid (0.036 g) in 1,2-dimethoxyethane (5.0 ml), ethanol (0.4 ml) and 2 M aqueous sodium carbonate solution (0.8 ml) with tetrakis(triphenylphosphine)palladium (0.023 g) to obtain the desired compound (0.058 g) as a brownish foam. MS (ISN): 548.3 (M−H)−

Sources & evidence

ORD record
ord-d8fb4e9db87b42eaa67fa07702573d58
Source dataset
uspto-grants-2012_04
Patent number
US08158655B2

Reaction notes

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